| Record Information |
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| Version | 2.0 |
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| Created at | 2021-01-05 20:08:26 UTC |
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| Updated at | 2021-07-15 17:06:52 UTC |
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| NP-MRD ID | NP0010716 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Penicacid B |
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| Provided By | NPAtlas |
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| Description | (3S)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hex-4-enoic acid belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Penicacid B is found in Penicillium. Based on a literature review very few articles have been published on (3S)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hex-4-enoic acid. |
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| Structure | [H]OC(=O)C([H])([H])[C@]([H])(O[C@@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])C(=C(/[H])C([H])([H])C1=C(O[H])C2=C(C(=C1OC([H])([H])[H])C([H])([H])[H])C([H])([H])OC2=O)\C([H])([H])[H] InChI=1S/C23H30O12/c1-9(4-5-11-17(27)16-12(8-33-22(16)31)10(2)21(11)32-3)13(6-15(25)26)34-23-20(30)19(29)18(28)14(7-24)35-23/h4,13-14,18-20,23-24,27-30H,5-8H2,1-3H3,(H,25,26)/b9-4+/t13-,14+,18+,19-,20+,23-/m0/s1 |
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| Synonyms | | Value | Source |
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| (3S)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hex-4-enoate | Generator | | alpha-D-Glucopyranosyl-4'-O-mpa | MeSH |
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| Chemical Formula | C23H30O12 |
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| Average Mass | 498.4810 Da |
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| Monoisotopic Mass | 498.17373 Da |
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| IUPAC Name | (3S,4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hex-4-enoic acid |
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| Traditional Name | (3S,4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hex-4-enoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C(C)C2=C(C(=O)OC2)C(O)=C1CC=C(C)[C@H](CC(O)=O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
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| InChI Identifier | InChI=1S/C23H30O12/c1-9(4-5-11-17(27)16-12(8-33-22(16)31)10(2)21(11)32-3)13(6-15(25)26)34-23-20(30)19(29)18(28)14(7-24)35-23/h4,13-14,18-20,23-24,27-30H,5-8H2,1-3H3,(H,25,26)/t13-,14+,18+,19-,20+,23-/m0/s1 |
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| InChI Key | WYXRFIJAMXLLNA-PAXYZUOBSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acyl glycosides |
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| Direct Parent | Fatty acyl glycosides of mono- and disaccharides |
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| Alternative Parents | |
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| Substituents | - Fatty acyl glycoside of mono- or disaccharide
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Isobenzofuranone
- Phthalide
- Isocoumaran
- Anisole
- Medium-chain fatty acid
- Alkyl aryl ether
- Branched fatty acid
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Sugar acid
- Dicarboxylic acid or derivatives
- Fatty acid
- Benzenoid
- Monosaccharide
- Unsaturated fatty acid
- Oxane
- Vinylogous acid
- Lactone
- Secondary alcohol
- Carboxylic acid ester
- Polyol
- Organoheterocyclic compound
- Carboxylic acid derivative
- Oxacycle
- Ether
- Acetal
- Carboxylic acid
- Primary alcohol
- Alcohol
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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